I'll tel you when it counts
There's this Orvis affiliated shop that I've been to a number of times.
As you all might realize, I'm not one to dress the part and in all the times that I've been in this shop never once has anyone ever spoken to me.
I get ignored like I wasn't even there.
The only time that anyone payed any attention to me at all was one day when they were having a tent sale.
A guy followed me around the whole time (never speaking) to make sure that I didn't steal anything.
I like to wear waders that don't leak, a vest that holds everything conveniently and fits well, an extremely old and torn up t-shirt or a really faded out long-sleeved shirt (they just feel comfortable to me), a hat with a big bill to shield the sun and good sunglasses. That about does it for me. Any other money I spend will be on more gear that actually catches fish!
I don't believe their is a fly fishing style in the fashion sense with respect to "Looking the part". When your on the water you aren't sporting an outfit, you wouldn't take your waders with you when buying a chest pack so you could see how well they looked together, we use equipment.
When someone "looks the part of a good fly fisherman" it's not defined by the appearance, type or brand of their equipment, its based on someones ability to skillfully use that equipment.
I wouldn't say to the person I'm fishing with, "Wow check out that guy downstream, he has a chest pack with a matching wading jacket...must be a guide or something". Someone "looking the part" or defined as a good fly fisherman in my mind would be if I witnessed a guy working he way downstream and on the first attempt picking off every riser he sees casting a seemingly perfect loop at 100 yards while nailing the presentation in every situation he encounters.
"I was born to fish" Lee Wulff
"There's more B.S. in fly fishing then there is in a Kansas feedlot." Lefty Kreh
" It ain't over till it's over." Yogi Berra
"Your not old,you've simply acquired a patina." Swirlchaser
I resemble that! I guess its like every other sport, and sometimes if you think you are being nonconformist or at least make a point of being nonconformist than you actually are trying to make an image of some sort. This just goes in circles. Someone wrote earlier up that there is huge enhancement in using what works for you. I think I like that the best. I'm over 50, I don't so much care anymore. Clean, simple, what works...etc.
Ive picked up some nice stuff and upgraded over the years as budget allowed, but do sometimes use my Redington Crosswater reel that I bought ~5 years ago for $9 on closeout when they changed the look of the holes or something on the fiber/plastic reel. This reel has or at least at the time had interchangeable drag components and bearing assy with their models costing ~$100 or more. Its mostly a backup, but if I'm going to be climbing up and down very many rocky hill sides, having this reel takes some of the pressure off not wanting to dent something nicer, and it does make it easier to set your rig down when all that is around you are beautiful Sierra granite boulders. But if anyone cares to notice, it does seem out of place on a nicer rod.
When I was tying flies commercially, there was local fellow who purchased flies from me occasionally for trips. He stopped by the house once to pick up some flies, and his attire was IMO, quite appropriate for a day out on the bay fishing. Otherwise, he looked like a bum! His clothes were badly wrinkled, and there was a few stains, & obvious wear. He however looked very comfortable!
This fellow owns a very large local real estate business & is a very rich man, a multi-millionaire who can afford anything he wishes to wear.
Great guy, avid fly angler too! His attire had nothing to do with anything except it was what he was comfortable in wearing. I've seen him in his business attire, and he's a sharp dresser!
Once in a local tackle shop, one I supplied with flies at the time, the owner pointed out an older fellow who was browsing some terminal tackle. He looked like a typical hard working fellow who could have been anyone in the area. Faded & worn jeans, an old worn flannel shirt & a worn hat. This man was also a very rich man. A local contracting legend who had built one of the most well designed communities in the area & who's work had a huge impact on the Inner Harbor area in Baltimore. He could also afford to wear anything he wanted.
Clothing or gear does not always tell the whole story. As the saying goes, never judge a book by it's cover!
I make a point to never try to judge anyone by their appearance, especially when it comes to fishing attire.